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Synthesis and Structure of Some Azo Coupled Cyclic beta-Enaminones
Authors: Šimůnek Petr | Lusková Lucie | Svobodová Markéta | Bertolasi Valerio | Lyčka Antonín | Macháček Vladimír
Year: 2007
Type of publication: článek v odborném periodiku
Name of source: Magnetic Resonance in Chemistry
Publisher name: John Wiley & Sons Ltd.
Place: Chichester
Page from-to: 330-339
Titles:
Language Name Abstract Keywords
cze Příprava a struktura některých azokopulovaných cyklických beta-enaminonů Reakcí 3-fenylaminocyklopent-2-en-1-onu s 4-methyl, 4-methoxy a 4-chlorbenzendiazonium-tetrafluorboráty byly připraveny azokopulační produkty 3a-c. Bylo zjištěno, že tyto sloučeniny existují jak v roztoku CDCl3, tak i v pevné fázi prakticky jako (E)-3-fenylamino-2-(4-subst.fenyldiazenyl)cyklopent-2-en-1-ony s N?H???N intramolekulární vodíkovou vazbou. Substituce na diazoniové soli nemá vliv na polohu tautomerní rovnováhy. Sloučeniny 4a,b vzniklé reakcí 3-fenylamino-1H-inden-1-onu s 4-methylbenzen nebo benzendiazonium-tetrafluorborátem jsou v roztoku CDCl3 i v pevné fázi jako hydrazosloučeniny. V roztoku tvoří tři formy, z nichž dvě byly identifikovány jako E/Z izomery lišící se typem vodíkových vazeb. Sloučenina 5 vzniklá reakcí 3-amino-5,5-dimethylcyklohex-2-en-1-onu s 4-methoxybenzendiazonium-tetrafluorborátu byla převedena na stabilní hydrochlorid 5?HCl stáním v chloroformu; tento produkt vykazuje vysoký stupeň delokalizace kladného náboje. Její struktura byla studována X-ray. 1H, 13C, 15N NMR, azokopulace, tautomerie, enaminony, X-Ray
eng Synthesis and Structure of Some Azo Coupled Cyclic beta-Enaminones The reaction of 3-phenylaminocyclopent-2-en-1-one with 4-methyl, 4-methoxy and 4-chlorobenzenediazonium tetrafluoroborates was used to prepare the azo coupling products 3a-c. It was found out that these compounds are present in both CDCl3 solution and solid phase practically exclusively as (E)-3-phenylamino-2-(4-subst.phenyldiazenyl)cyclopent-2-en-1-ones with N?H???N intramolecular hydrogen bond. The substitution of the phenyl residue of the diazonium salt has no effect on the position of the tautomeric equilibrium. On the other hand, the compounds 4a,b formed by the reaction of 3-phenylamino-1H-inden-1-one with 4-methylbenzene- or benzenediazonium tetrafluoroborates exist in CDCl3 solution and in solid phase as hydrazone compounds. In the solution they occur as a mixture of three forms, out of which two were identified as E/Z isomers with different types of hydrogen bonds. Compound 5 formed by the reaction of 3-amino-5,5-dimethylcyclohex-2-en-1-one with 4-methoxybenzenediazonium tetrafluoroborate is converted into a stable hydrochloride 5?HCl on standing in CHCl3 solution; this product exhibits a high degree of delocalisation of the positive charge. Its structure was studied by means of X-ray. 1H, 13C, 15N NMR, azo coupling, tautomerism, enaminones, X-Ray, NMR

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